ASYMMETRIC-SYNTHESIS OF ALLYLSILANES BY PALLADIUM-CATALYZED ASYMMETRIC REDUCTION OF ALLYLIC CARBONATES WITH FORMIC-ACID

被引:53
作者
HAYASHI, T [1 ]
IWAMURA, H [1 ]
UOZUMI, Y [1 ]
机构
[1] HOKKAIDO UNIV,GRAD SCH PHARMACEUT SCI,SAPPORO 060,JAPAN
关键词
D O I
10.1016/S0040-4039(00)76975-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reduction of 3-alkyl-3-trialkylsilyl-2-propenyl methyl carbonates with formic acid and 1,8-bis(dimethylamino)naphthalene in the presence of a palladium catalyst (3 mol %) coordinated with (R)-3-diphenylphosphino-3'-methoxy-4 4'-biphenanthryl (MOP-phen) gave optically active allylsilanes (3-alkyl-3-trialkylsilyl-1 -propenes) of up to 91% ee.
引用
收藏
页码:4813 / 4816
页数:4
相关论文
共 33 条
[1]  
BRUNNER H, 1988, SYNTHESIS-STUTTGART, P645
[2]  
BRUNNER H, 1988, TOP STEREOCHEM, V18, P129
[3]   ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].
CONSIGLIO, G ;
WAYMOUTH, RM .
CHEMICAL REVIEWS, 1989, 89 (01) :257-276
[4]   SOME USES OF SILICON-COMPOUNDS IN ORGANIC-SYNTHESIS [J].
FLEMING, I .
CHEMICAL SOCIETY REVIEWS, 1981, 10 (01) :83-111
[5]  
Fleming I., 1991, COMPREHENSIVE ORGANI, P563
[6]  
HAYASHI T, 1985, CHEM SCRIPTA, V25, P61
[7]   OPTICALLY-ACTIVE ALLYLSILANES .3. ANTI STEREOCHEMISTRY IN PROTODESILYLATION OF AN OPTICALLY-ACTIVE ALLYLSILANE WITH TRIFLUOROACETIC ACID-D [J].
HAYASHI, T ;
ITO, H ;
KUMADA, M .
TETRAHEDRON LETTERS, 1982, 23 (44) :4605-4606
[8]   OPTICALLY-ACTIVE ALLYLSILANES .4. ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES WITH AN OPTICALLY-ACTIVE ALLYLSILANE [J].
HAYASHI, T ;
KONISHI, M ;
KUMADA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (02) :281-282
[9]  
HAYASHI T, 1982, J AM CHEM SOC, V104, P4963, DOI 10.1021/ja00382a046
[10]   OPTICALLY-ACTIVE CYCLIC ALLYLSILANES .7. PREPARATION BY ASYMMETRIC HYDROSILYLATION AND ANTI STEREOCHEMISTRY IN SE' REACTIONS [J].
HAYASHI, T ;
KABETA, K ;
YAMAMOTO, T ;
TAMAO, K ;
KUMADA, M .
TETRAHEDRON LETTERS, 1983, 24 (50) :5661-5664